Juan Ponce de Leon came to the Americas in 1513 searching for the fountain of youth. He never found it, but he apparently left behind the belief that old bones can be rejuvenated, as Microsoft seems to be chasing th same elixir with its proposed acquisition of Yahoo!.

Microsoft isn't a turkey, but a profitable, boring mastodon that entertains fantasies about being able to fly. Yahoo, for its part, is an ageing hippy who invented hang- gliding but aspired to fly 747s and then discovered that he wasn't very good at it. The mastodon hopes that by employing the hippy it will learn to hang-glide. The hippy's feelings about the whole deal are plain for all to see.

Is a combination of the two going to work? I think increasingly highly of Yahoo! but it's Microsoft's intransigence toward new ideas that offers the most resistance to the deal working.

In Silicon Valley today, software is increasingly delivered as a Web service, it is often put together by teams of programmers who might be scattered on three continents, it's often free to users, and Web surfers usually do the testing soon after the first prototype is complete.

By contrast, Microsoft has long been a software engineering culture in which huge projects like Windows Vista are developed and tested by teams of hundreds, and whose completion time is measured in a large fraction of decades.

Microsoft could learn a lesson from a different explorer to the Americas, Hernan Cortez, whose policy was to "burn the boats." It's understandable that Microsoft would cling to its profitable past. That past churns out billions of dollars in profits each quarter. Who wouldn't want that?

But Microsoft is completely irrelevant in the 21st Century of software. If it wants to return to its money-minting exercise, it needs to stop seeking to slap a new face on old businesses and instead build new businesses with new people and new business models. Easier said than done, but who said it should be easy to make billions?

About the author

Matt Asay is chief operating officer at Canonical, the company behind the Ubuntu Linux operating system. Prior to Canonical, Matt was general manager of the Americas division and vice president of business development at Alfresco, an open-source applications company. Matt brings a decade of in-the-trenches open-source business and legal experience to The Open Road, with an emphasis on emerging open-source business strategies and opportunities. He is a member of the CNET Blog Network and is not an employee of CNET. You can follow Matt on Twitter @mjasay.
See full bio